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Writing and Kayaking Retreat with Jenny O’Connell

Take ample time for both guided and independent writing as you explore Maine's islands!

Quick Details

Workshop Participant

A Three-Day Retreat on Maine’s Island Trail

There are more than 300 islands in Casco Bay, creating endless possibilities for exploration by sea kayak – and creative exploration! This three-day trip features personalized creative writing sessions led by award-winning outdoor writer Jenny O’Connell. 

Nestled within the many islands of Casco Bay are some of our favorite campsites on the Maine Island Trail. Every trip is different, with a route tailored to fit the conditions and the group, but it’s common to visit Jewell Island, with miles of trails, stunning cliffs, wild beaches, or Whaleboat Island, a rarely-visited, forested preserve beside the open ocean, or the smaller, isolated gem of Bangs Island. 

Where You’ll Paddle

You’ll start out kayaking along the working waterfront of Portland harbor, past the scenic hamlets of the inner islands and past the exposed shorelines of the bay’s wildest islands. Along the way, you’ll pass hidden beaches and rugged, rocky headlands. On the first night your group will settle into camp together, the place that will be your home together for the next two days. On the second day you’ll leave camp set up, allowing more time to dive into writing, and to enjoy a short day paddle around your island home, or to another island nearby. Finally, on the third day, after some final activities together, you will depart to return to the main land. 

As you paddle across the bay you’ll encounter abundant wildlife like seals and seabirds, and you’ll experience a diverse range of marine environments, from exposed ocean shorelines to the calm waters of coastal estuaries. You’ll also witness fascinating remnants of the past, like abandoned forts and centuries-old lighthouses, and glimpses of the working waterfront that is the heart of Maine’s island communities.

The itinerary will depend on the conditions and the group. You can expect to paddle for several hours each day, with many breaks along the way. There will also be plenty of time for writing, exploring and relaxing on the islands. Your guide will choose a route that takes maximum advantage of the wind direction and tidal currents, while ensuring that the group moves at a pace that is comfortable for all participants.

Creative Writing

Guided writing sessions are woven into the trip experience and crafted to fit the creative desires of the group. You don’t need to identify as a writer to participate (though if you do, that’s great too!) – just show up with a notebook, a few good pens, and an open mind and we’ll take care of the rest. All genres and experience levels are welcome! 

We’ll be using creative writing to deepen our connection with our natural surroundings, and to find and develop the stories we want to tell. Each session will include creative warm-ups, craft tips, a longer period of writing time to drop into creative flow, and an opportunity to share excerpts of your work with the group. 

At certain points during the trip, Jenny will also be available for one-on-one check-ins for advanced writers who want to elevate their craft, or for beginner and intermediate writers who are looking for their next step. On our last night, we’ll share our work out loud with each other at a celebratory reading. 

More Info

CLICK HERE for a detailed packing list and tips on packing a sea kayak!

For an depth sample trip itinerary of one of our regular Casco Bay Traverse paddles, CLICK HERE!

About Jenny

Jenny O’Connell is a writer, outdoor guide, and teacher of creative writing. Her debut adventure memoir, Finding Petronella, traces her solo trek across Finland following the footsteps of a female legend beyond the Arctic Circle. Jenny’s award-winning nonfiction has appeared in magazines across the country, including Creative Nonfiction, Down East, Backcountry, Maine Magazine, and Appalachia Journal. Her sixteen years as an outdoor guide have brought her all over the globe leading backpacking, sea kayaking, cultural exchange, winter adventure, and river expeditions from the Peruvian Andes to the wild waters of her home state of Maine. She never leaves home without a trusty pair of adventure pants and a waterproof ukulele. 

A photo of guide-writing coach Jenny O'Connell in a field